Water-soluble manganese carbonyl compound carbon monoxide releasing agent, its preparation method and application

Abstract

The application discloses a water-soluble manganese carbonyl compound carbon monoxide releasing agent, and the chemical formula is shown in the following formula: compounds 1-compound 8 in the application can be decomposed and CO can be released under the action of visible light, and can be used as a light-induced carbon monoxide releasing molecule.

Description

TECHNICAL FIELD

[0001] The present application relates to the field of carbon monoxide releasing agents. More particularly, the present application relates to a water-soluble manganese carbonyl compound carbon monoxide releasing agent, its preparation method and application. BACKGROUND

[0002] It is well known that carbon monoxide (CO) is a toxic gas, known as the "silent killer". But researchers have found that the human body produces a small amount of CO (about 10 mL / day) every day, and this endogenous CO is mainly derived from the decomposition of hemoglobin (about 85%). Moreover, it is similar to nitric oxide (NO) and is an important messenger molecule in the body, which is involved in the regulation of many physiological and pathological processes in the body. Animal experiment results show that inhaling a small amount of CO can reduce the response of pulmonary hypertension, and it can also protect important organs such as the brain, heart, lungs and liver when the body is ischemic and hypoxic or organ transplantation.

[0003] Since CO is beneficial to the human body, scientists want to use it for clinical treatment. Early studies were carried out by inhaling CO at a certain concentration, but CO is a toxic gas, and improper use can harm the human body. In order to safely and effectively use the biological small molecule CO, the concept of carbon monoxide-releasing molecules (CORMs) is proposed, that is, to use CO carriers to achieve the release of small doses of CO at a specific site. Transition metal carbonyl compounds are a class of metal organic compounds containing carbonyl groups. The carbonyl groups in these compounds can be decomposed to release CO under certain conditions, and they can also load multiple CO. Currently, the compounds related to CORMs are mainly some transition metal carbonyl compounds, mainly focusing on Ru, Mn, Mo, Re, Fe and other metal elements. Therefore, transition metal carbonyl compounds have become the focus of CORMs research. Although there are many types of CORMs reported at present, only a few of them can be truly used for clinical research, the main reason being that as an ideal CORMs drug, it needs to have good water solubility, biological safety and release controllability characteristics. Therefore, the water solubility of CORMs directly affects its pharmaceutical prospects. At present, the progress of CORMs research in this regard is still very slow, and more water-soluble compounds need to be synthesized. Manganese is an essential trace element for the human body and plays an important role in maintaining human health. Therefore, manganese-based CORMs may have good biological compatibility. It is of great significance to study manganese-based CORMs with water solubility to release CO under certain conditions. SUMMARY

[0004] To achieve these objects and other advantages in accordance with the purpose of the application, one aspect, a preferred embodiment of the present application provides a water-soluble manganese carbonyl compound carbon monoxide releasing agent, which is represented by the following chemical formula:

[0005]

[0006] The main chain structure of the chemical 1-4 is less than one benzene ring compared with the main chain structure of the chemical 5-8.

[0007] Another aspect, a preferred embodiment of the present application also provides a preparation method of a water-soluble manganese carbonyl compound carbon monoxide releasing agent, which comprises the following steps:

[0008] Dissolve the aniline derivative and pyridine-2-carboxaldehyde or quinoline-2-carboxaldehyde in the solvent, then add the manganese pentacarbonyl bromide, and react in the dark under reflux. Stop heating after the reaction is completed by TLC monitoring. The obtained product is obtained by suction filtration or recrystallization to obtain the target compound.

[0009] Preferably, when the water-soluble manganese carbonyl compound carbon monoxide releasing agent is any one of the chemical 1-4, the preparation process is as follows:

[0010] Dissolve the sodium p-aminobenzenesulfonate / p-aminobenzoic acid / p-aminointerbenzene dicarboxylic acid / p-aminosalicylic acid and pyridine-2-carboxaldehyde in the solvent, then add the manganese pentacarbonyl bromide, and react in the dark under heating to obtain the target product, the water-soluble manganese carbonyl compound carbon monoxide releasing agent;

[0011] When the water-soluble manganese carbonyl compound carbon monoxide releasing agent is any one of the chemical 5-8, the preparation process is as follows:

[0012] Dissolve the sodium p-aminobenzenesulfonate / p-aminobenzoic acid / p-aminointerbenzene dicarboxylic acid / p-aminosalicylic acid and pyridine-2-carboxaldehyde in the solvent, then add the manganese pentacarbonyl bromide, and react in the dark under heating to obtain the target product, the water-soluble manganese carbonyl compound carbon monoxide releasing agent.

[0013] Preferably, when the water-soluble manganese carbonyl compound carbon monoxide releasing agent is any one of the chemical 1-4, the preparation process is as follows:

[0014] Dissolve 0.3 mmol of sodium p-aminobenzenesulfonate / p-aminobenzoic acid / p-aminointerbenzene dicarboxylic acid / p-aminosalicylic acid and 0.3 mmol of pyridine-2-carboxaldehyde in 4 mL of methanol, then add 0.3 mmol of manganese pentacarbonyl bromide, and react in the dark under reflux. Stop heating after the reaction is completed by TLC monitoring. After cooling, remove the solvent by rotary evaporation. The obtained product is further recrystallized by methanol and diethyl ether to obtain the target product;

[0015] When the water-soluble manganese carbonyl compound carbon monoxide releasing agent is any one of compounds 5-8, it is prepared as follows:

[0016] 0.3 mmol of sodium p-aminobenzenesulfonate / p-aminobenzoic acid / m-aminobenzoic acid / m-aminosalicylic acid and 0.3 mmol of quinoline-2-carboxaldehyde are dissolved in 4 mL of methanol at the same time, and then 0.3 mmol of manganese pentacarbonyl bromide is added thereto, and the solution is reacted under reflux in the dark, and the reaction is stopped by heating after the reaction is completed by TLC monitoring. The obtained solution is further recrystallized from methanol and diethyl ether to obtain the target product.

[0017] In another aspect, a preferred embodiment of the present application also provides the use of the water-soluble manganese carbonyl compound carbon monoxide releasing agent in the release of CO.

[0018] The present application at least includes the following beneficial effects: the water-soluble manganese carbonyl compound carbon monoxide releasing agent prepared by the present application has good water solubility, can release CO by visible light induction, and can be synthesized by a one-step method.

[0019] Other advantages, objects, and features of the present application will be understood by those skilled in the art from the following description, and will be further understood by those skilled in the art through research and practice of the present application. BRIEF DESCRIPTION OF DRAWINGS

[0020] Figure 1 NMR spectrum of compound 1;

[0021] Figure 2 NMR spectrum of compound 2;

[0022] Figure 3 NMR spectrum of compound 3;

[0023] Figure 4 NMR spectrum of compound 4;

[0024] Figure 5 NMR spectrum of compound 5;

[0025] Figure 6 NMR spectrum of compound 6;

[0026] Figure 7 NMR spectrum of compound 7;

[0027] Figure 8 NMR spectrum of compound 8;

[0028] Figure 9 Infrared spectrum of compound 1 over time under blue light irradiation;

[0029] Figure 10Figure 2 is a plot of the infrared spectrum of compound 1 over time under blue light irradiation;

[0030] Figure 11 Figure 3 is a plot of the infrared spectrum of compound 2 over time under blue light irradiation;

[0031] Figure 12 Figure 4 is a plot of the infrared spectrum of compound 2 over time under green light irradiation;

[0032] Figure 13 Figure 5 is a plot of the infrared spectrum of compound 2 over time under red light irradiation;

[0033] Figure 14 Figure 6 is a plot of the infrared spectrum of compound 3 over time under blue light irradiation;

[0034] Figure 15 Figure 7 is a plot of the infrared spectrum of compound 3 over time under green light irradiation;

[0035] Figure 16 Figure 8 is a plot of the infrared spectrum of compound 3 over time under red light irradiation;

[0036] Figure 17 Figure 9 is a plot of the infrared spectrum of compound 4 over time under blue light irradiation;

[0037] Figure 18 Figure 10 is a plot of the infrared spectrum of compound 4 over time under green light irradiation;

[0038] Figure 19 Figure 11 is a plot of the infrared spectrum of compound 4 over time under red light irradiation;

[0039] Figure 20 Figure 12 is a plot of the infrared spectrum of compound 5 over time under blue light irradiation;

[0040] Figure 21 Figure 13 is a plot of the infrared spectrum of compound 5 over time under green light irradiation;

[0041] Figure 22 Figure 14 is a plot of the infrared spectrum of compound 6 over time under blue light irradiation;

[0042] Figure 23 Figure 15 is a plot of the infrared spectrum of compound 6 over time under green light irradiation;

[0043] Figure 24 Figure 16 is a plot of the infrared spectrum of compound 6 over time under red light irradiation;

[0044] Figure 25 Figure 17 is a plot of the infrared spectrum of compound 7 over time under blue light irradiation;

[0045] Figure 26 Figure 18 is a plot of the infrared spectrum of compound 7 over time under green light irradiation;

[0046] Figure 27 Figure 7 is a graph showing the change in infrared spectrum of compound 7 over time under red light irradiation;

[0047] Figure 28 Figure 8 is a graph showing the change in infrared spectrum of compound 8 over time under blue light irradiation;

[0048] Figure 29 Figure 9 is a graph showing the change in infrared spectrum of compound 8 over time under green light irradiation;

[0049] Figure 30 Figure 10 is a graph showing the change in infrared spectrum of compound 8 over time under red light irradiation;

[0050] Figure 31 Figure 11 is a graph showing the change in ultraviolet absorption peak of a deoxymyoglobin solution after adding compound 1 under LED blue light irradiation; Figure 32 Figure 12 is a graph showing the change in ultraviolet absorption peak of a deoxymyoglobin solution after adding compound 1 under LED green light irradiation DETAILED DESCRIPTION

[0051] The present application will be further described with reference to the drawings, in which:

[0052] The following description is provided so as to enable any person skilled in the art to practice the application. The preferred embodiments described herein are only examples of the application and various modifications can be made by those skilled in the art without departing from the spirit and scope of the application. The general principles defined herein can be applied to other embodiments, variations, modifications, equivalents and other technical solutions without departing from the spirit and scope of the application.

[0053] It should be understood that the term "one" should be understood as "at least one" or "one or more", that is, in one embodiment, the number of one element can be one, and in another embodiment, the number of the element can be multiple, and the term "one" cannot be understood as a limitation on the number.

[0054] Example 1

[0055] The synthesis method of compound 1 is as follows: sodium p-aminobenzenesulfonate (57 mg, 0.3 mmol) and pyridine-2-carboxaldehyde (31 mg, 0.3 mmol) are added to a 50 mL round-bottom flask and dissolved in 4 mL of methanol, then manganese pentacarbonyl bromide (80 mg, 0.3 mmol) is added, and the solution is reacted under reflux in the dark, and the reaction is stopped by heating after the reaction is monitored by TLC to end, and the solvent is removed by rotary evaporation after the reaction solution is cooled, and the resulting product is further recrystallized from methanol and diethyl ether to obtain compound 1.

[0056] The structural formula of compound 1 is as follows:

[0057] The NMR result of compound 1 is as follows: 1 H NMR (400 MHz, DMSO) δ 9.20 (s, 1H), 8.89 (s, 1H), 8.26 (s, 2H), 7.78 (s, 3H), 7.48 (s, 2H).

[0058] Example 2

[0059] The synthesis method of compound 2 is as follows: p-aminobenzoic acid (41 mg, 0.3 mmol) and pyridine-2-carboxaldehyde (31 mg, 0.3 mmol) are added to a 50 mL round-bottom flask and dissolved in 4 mL of methanol, then manganese pentacarbonyl bromide (80 mg, 0.3 mmol) is added, and the solution is reacted under reflux and in the dark. The reaction is stopped after the reaction is completed by TLC monitoring, and the reaction solution is cooled and the solvent is removed by rotary evaporation. The resulting product is further recrystallized with methanol and diethyl ether to obtain compound 2.

[0060] The structural formula of compound 2 is as follows:

[0061] The NMR result of compound 2 is as follows: 1 H NMR (400 MHz, DMSO) δ 13.23 (s, 1H), 9.23 (s, 1H), 8.95 (s, 1H), 8.27 (s, 2H), 8.13 (s, 2H), 7.80 (s, 1H), 7.63 (s, 2H).

[0062] Example 3

[0063] The synthesis method of compound 3 is as follows: p-aminobenzoic acid (41 mg, 0.3 mmol) and pyridine-2-carboxaldehyde (31 mg, 0.3 mmol) are added to a 50 mL round-bottom flask and dissolved in 4 mL of methanol, then manganese pentacarbonyl bromide (80 mg, 0.3 mmol) is added, and the solution is reacted under reflux and in the dark. The reaction is stopped after the reaction is completed by TLC monitoring, and the reaction solution is cooled and the solvent is removed by rotary evaporation. The resulting product is further recrystallized with methanol and diethyl ether to obtain compound 3.

[0064] The structural formula of compound 3 is as follows:

[0065] The NMR result of compound 3 is as follows: 1H NMR (400 MHz, DMSO) δ 13.62 (s, 1H), 9.24 (d, J = 5.5 Hz, 1H), 9.03 (s, 1H), 8.51 (s, 1H), 8.34 (s, 2H), 8.27 (d, J = 4.4 Hz, 2H), 7.86 - 7.76 (m, 1H).

[0066] Example 4

[0067] The synthesis of compound 4 is as follows: in a 50 mL round bottom flask, add p-aminosalicylic acid (46 mg, 0.3 mmol) and pyridine-2-carboxaldehyde (31 mg, 0.3 mmol) and dissolve in 4 mL of methanol, then add manganese pentacarbonyl bromide (80 mg, 0.3 mmol), the solution is reacted under reflux state in the dark, stop heating after the end of the reaction monitored by TLC, the reaction solution is cooled and the solvent is removed by rotary evaporation, the resulting product is further recrystallized from methanol and diethyl ether to obtain compound 4.

[0068] The structural formula of compound 4 is as follows:

[0069] The nuclear magnetic resonance results of compound 4 are as follows: 1 H NMR (400 MHz, DMSO) δ 9.22 (d, J = 5.3 Hz, 1H), 8.92 (s, 1H), 8.25 (s, 2H), 8.03 (s, 1H), 7.85 - 7.76 (m, 2H), 7.18 (d, J = 8.7 Hz, 1H).

[0070] Example 5

[0071] The synthesis of compound 5 is as follows: in a 50 mL round bottom flask, add sodium p-aminobenzenesulfonate (57 mg, 0.3 mmol) and quinoline-2-carboxaldehyde (47 mg, 0.3 mmol) and dissolve in 4 mL of methanol, then add manganese pentacarbonyl bromide (80 mg, 0.3 mmol), the solution is reacted under reflux state in the dark for 3-5 h, stop heating after the end of the reaction monitored by TLC, the resulting solution is removed from the solvent and further recrystallized from methanol and diethyl ether to obtain compound 5.

[0072] The structural formula of compound 5 is as follows:

[0073] The nuclear magnetic resonance results of compound 5 are as follows: 1 H NMR (400 MHz, DMSO) δ 9.20 (s, 1H), 8.85 (s, 2H), 8.29 (d, J = 19.1 Hz, 2H), 8.14 (s, 2H), 7.91 (s, 2H), 7.52 (s, 2H).

[0074] Example 6

[0075] The synthesis of compound 6 is as follows: p-Aminobenzoic acid (41 mg, 0.3 mmol) and quinoline-2-carboxaldehyde (47 mg, 0.3 mmol) were added in a 50 mL round bottom flask and dissolved in 4 mL of methanol, then manganese pentacarbonyl bromide (80 mg, 0.3 mmol) was added, the solution was refluxed and protected from light for 3-5 h, the reaction was stopped by removing the heat after the reaction was monitored by TLC, the resulting solution was further recrystallized from methanol and diethyl ether after removing the solvent to obtain compound 6.

[0076] The structural formula of compound 6 is as follows:

[0077] The NMR result of compound 6 is as follows: 1 H NMR (400 MHz, DMSO), δ

[0078] 13.25 (s, 1H), 9.29 (s, 1H), 8.90 (dd, J = 25.5, 8.5 Hz, 2H), 8.33 (dd, J = 20.9, 8.1 Hz, 2H),

[0079] 8.26 - 8.09 (m, 3H), 7.96 (t, J = 7.4 Hz, 1H), 7.71 (s, 2H).

[0080] Example 7

[0081] The synthesis of compound 7 is as follows: m-Aminobenzoic acid (41 mg, 0.3 mmol) and quinoline-2-carboxaldehyde (47 mg, 0.3 mmol) were added in a 50 mL round bottom flask and dissolved in 4 mL of methanol, then manganese pentacarbonyl bromide (80 mg, 0.3 mmol) was added, the solution was refluxed and protected from light for 3-5 h, the reaction was stopped by removing the heat after the reaction was monitored by TLC, the resulting solution was further recrystallized from methanol and diethyl ether after removing the solvent to obtain compound 7.

[0082] The structural formula of compound 7 is as follows:

[0083] The NMR result of compound 7 is as follows: 1 H NMR (400 MHz, DMSO), δ 13.42 (s, 1H), 9.31 (s, 1H), 8.89 (dd, J = 19.9, 8.3 Hz, 2H), 8.32 (dd, J = 18.4, 8.0 Hz, 2H), 8.18 (dd, J = 16.6, 8.8 Hz, 2H), 8.08 (s, 1H), 7.96 (t, J = 7.3 Hz, 1H), 7.82 (d, J = 47.7 Hz, 2H).

[0084] Example 8

[0085] The synthesis of compound 8 is as follows: m-aminosalicylic acid (46 mg, 0.3 mmol) and quinoline-2-carboxaldehyde (47 mg, 0.3 mmol) were added in a 50 mL round bottom flask and dissolved in 4 mL methanol, then manganese pentacarbonyl bromide (80 mg, 0.3 mmol) was added, the solution was refluxed and protected from light for 3-5 h, the reaction was stopped by removing the heat after the reaction was monitored by TLC, the resulting solution was further recrystallized from methanol and diethyl ether to obtain compound 8.

[0086] The structural formula of compound 8 is as follows:

[0087] The nuclear magnetic resonance results of compound 8 are as follows: 1 H NMR (400 MHz, DMSO) δ 9.20 (s, 1H), 8.88-8.79 (m, 2H), 8.25 (t, J = 8.0 Hz, 2H), 8.15-8.09 (m, 1H), 8.03 (s, 1H), 7.90 (t, J = 6.8 Hz, 1H), 7.80 (d, J = 8.4 Hz, 1H), 7.20 (d, J = 8.7 Hz, 1H).

[0088] Application of compound 9 in light-induced CO release:

[0089] Compounds 1-8 have good stability in the dark but are sensitive to light and can be used as light-induced carbon monoxide release agents. The CO release performance of these compounds was tested under visible light (LED blue, green or red light, 3W, 220V) irradiation.

[0090] Compound 1 is easily soluble in water, but water has a strong absorption at 1900-2000 cm -1 around, and the carbonyl infrared absorption peak is also at this position, so water as a solvent will interfere with the monitoring of the carbonyl peak. In order to exclude interference, the CO release of the compound was carried out in heavy water. As shown in Figure 9 and Figure 10 Compound 1 in heavy water shows two typical carbonyl characteristic peaks (2045 and 1952 cm -1 ). The absorbance of the characteristic peak is basically unchanged under light protection conditions, showing good stability. However, under the action of blue light, it will be significantly weakened and new absorption peaks will gradually appear (at 2029, 1990 and 1860 cm -1The appearance of new absorption peaks indicates that the compound is decomposed under blue light irradiation and new substances are produced. These carbonyl characteristic peaks can also gradually weaken under green light irradiation, but the decline is slower than under blue light. With the extension of irradiation time, two new peaks gradually appear at 2030 and 1937, indicating that the compound can also be decomposed under green light and new substances are produced. Under the above irradiation, bubbles are produced in the solution, which is the released CO.

[0091] Compound 2-4 can be dissolved in water, but the solubility is poor, and it is more soluble in DMSO, so the light-induced CO release of the compound is carried out in DMSO. As shown in Figures 11-19 , compound 2-4 in DMSO shows three typical carbonyl characteristic peaks (2025, 1936, 1918 cm -1 ), which gradually decrease under LED blue light, green light and red light. The decomposition mode of these compounds under blue light and green light is basically similar, that is, the three carbonyl characteristic peaks of the compound gradually decrease with the extension of irradiation time, and new peaks appear at 1949 and 1873 cm -1 . While under red light, the decomposition mode of the compound is only the decrease of the absorption peak, without the appearance of other new peaks.

[0092] The water solubility of compound 5 is lower than that of 1, and a small amount of DMSO is needed to help dissolve, so the CO release of the compound is carried out in a mixed solvent of heavy water and DMSO (volume ratio of 2:1). As shown in Figures 20-21 , compound 5 in the above mixed solvent shows two characteristic carbonyl peaks (2041 and 1943 cm -1 ), due to the influence of the solvent, a shoulder peak appears at 2033 cm -1 . Similarly, this absorption peak is very stable under light shielding conditions, and will rapidly decrease under blue light and green light irradiation, and finally produce three absorption peaks at 2028, 1933 and 1908 cm -1 . It indicates that the compound is decomposed and converted into new substances.

[0093] Compounds 6-9 can be dissolved in water, but the solubility is poor, so the CO release of the compound is carried out in DMSO. As shown in Figures 22-30 , these compounds have three carbonyl characteristic peaks at 2022, 1934 and 1922 cm -1 . Under the irradiation of LED blue light, green light or red light, these characteristic peaks gradually weaken, indicating that the compound is decomposed under light irradiation. The decomposition mode of compounds 6-9 under the above visible light irradiation is similar, only the decrease of the carbonyl characteristic peak is shown, without the appearance of new peaks.

[0094] In summary, compounds 1-8 can release CO under visible light, and can be used as photo-induced CO releasing molecules. Kinetic studies show that the decomposition of these compounds under light follows a first-order kinetic model. Table 1 shows the kinetic results of the photo-induced CO releasing of compounds 1-8. From the table, for the same compound, blue light is the most effective light source to promote the decomposition of the compound, followed by green light, and red light is the worst. Blue light is the most effective light source to promote the decomposition of the compound to release CO because it has higher energy. However, light with high energy has weak penetration of the skin, and it is difficult to produce practical applications. Red light with low energy has good penetration, and is the most effective light source for treatment. Among these compounds, the manganese compounds 6-8 containing quinoline group Schiff base ligand decompose faster than the manganese compounds containing pyridine group Schiff base ligand under red light, and can be used as low-energy light-induced CO releasing molecules.

[0095] Table 1 Kinetic results of the decomposition of compounds 1-8 under different LED visible light

[0096]

[0097] In addition, taking compound 1 as an example, the release of CO of the compound under light was qualitatively studied by myoglobin experiments. Figure 31 and Figure 32 Figure 2 is a diagram showing the change of the ultraviolet absorption peak of the deoxy-myoglobin solution after adding compound 1 under different LED light. The myoglobin experiment shows that the ultraviolet absorption of the deoxy-myoglobin does not change basically under the light shielding condition of compound 1, but the absorption peak at 560 nm gradually weakens under light, and two characteristic absorption peaks at 540 nm and 580 nm appear, which are the characteristic peaks of carbon-oxygen myoglobin, indicating that the CO decomposed by the compound is absorbed by the deoxy-myoglobin and converted into carbon-oxygen myoglobin. This process can qualitatively show that the compound can release CO under light, and can be used as a photo-induced CO releasing molecule (photoCORMs). Other compounds also have similar properties, and can release CO under light.

[0098] Although the embodiments of the present application have been disclosed as above, they are not limited to the application listed in the specification and the embodiments, and can be fully applied to various fields suitable for the present application, and other modifications can be easily realized by those skilled in the art, and therefore the present application is not limited to specific details and the figures shown and described herein, without departing from the general concept defined by the claims and the equivalent scope.

Claims

1. A water-soluble manganese carbonyl compound, characterized by, The chemical formula is as follows: 。 2. A process for producing a water-soluble manganese carbonyl compound as claimed in claim 1, characterized by, The method comprises the following steps: The aniline derivative and quinoline-2-carboxaldehyde are dissolved in a solvent, and then manganese pentacarbonyl bromide is added. The solution is reacted under reflux and in the dark, and the reaction is stopped after the reaction is completed by TLC monitoring. The obtained product is filtered or recrystallized to obtain the target compound.

3. The method for preparing the water-soluble manganese carbonyl compound according to claim 2, wherein, The sodium p-aminobenzenesulfonate / m-aminobenzoic acid / p-aminobenzoic acid / m-aminosalicylic acid and quinoline-2-carboxaldehyde are dissolved in a solvent, and then manganese pentacarbonyl bromide is added. The solution is reacted under reflux and in the dark, and the reaction is stopped after the reaction is completed by TLC monitoring. The obtained product is filtered or recrystallized to obtain the target product, the water-soluble manganese carbonyl compound.

4. The method for preparing the water-soluble manganese carbonyl compound according to claim 3, wherein, 0.3 mmol of sodium p-aminobenzenesulfonate / p-aminobenzoic acid / m-aminobenzoic acid / m-aminosalicylic acid and 0.3 mmol of quinoline-2-carboxaldehyde are simultaneously dissolved in 4 mL of methanol, and then 0.3 mmol of manganese pentacarbonyl bromide is added. The solution is reacted under reflux and in the dark, and the reaction is stopped after the reaction is completed by TLC monitoring. The obtained solution is further recrystallized from methanol and diethyl ether to obtain the target product.

5. The use of the water-soluble manganese carbonyl compound according to claim 1 in the preparation of a CO releasing agent.

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